


If it wasn't for this pesky gay thing.

by Dolavine



Series: spn_masquerade fills [5]
Category: Supernatural RPF
Genre: Awkward Sexual Situations, F/M, Het, self orgasm
Language: English
Status: Completed
Published: 2015-03-22
Updated: 2015-03-22
Packaged: 2018-03-19 02:02:20
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,103
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3592110
Author URL: https://archiveofourown.org/users/Dolavine/pseuds/Dolavine
Summary: <blockquote class="userstuff">
              <p>After a night of drinking, Jensen is curious about het sex and picks his best friend Danneel to experiment with.</p>
            </blockquote>





	If it wasn't for this pesky gay thing.

**Author's Note:**

> Written for spn_masquerade for the prompt: Jensen/Danneel first time hetero sex: Jensen is firmly gay but he’ll admit he is curious as to what all the fuss is about. He asks his best friend Danni to have sex with him. First time hetero sex, awkward, embarrassing not sure anyone comes and Jensen has his answer he’s not switching teams.

Jensen’s known he’s gay since he was seven years old when he developed his first crush on his best friend’s older brother. He was positive of it at thirteen when he couldn’t take his eyes off of most of the naked bodies in the gym locker room and absolutely sure when he kissed the captain of the high school football team before they beat each other off under the bleachers. It sort of sealed the deal when he couldn’t bring himself on prom night not to fuck his long time (beard) girlfriend in the expensive hotel room after extensively watching hetero porn to get it right. Yeah, he was quite sure he was a hundred percent gay.

He’s been friends with Danneel Harris for ages. They do everything together, share everything and spend hours exchanging sex stories. Although he’s has no desire to have a sexual relationship with Danneel, he thinks she’s the prettiest woman he knows and if he did ever want to switch sides, it would definitely be with her.

So one night when they’re out at a club and Jensen is being Dannee’s wingman but failing miserably at it, they drink a little too much and start over-sharing about what they like sexually. They discover that they have two favorite things, giving blowjobs and being fingered. 

“Oh god, I love it when a guy’s got his fingers buried deep inside of me. When they crook their fingers and pull just to the edge before pushing back in. UNGH! Yeah. That’s the absolute best.” Dannee gushes.

Jensen thinks about it, knows that he likes the same thing. “And when they go really, really deep until their pressed so tight against your body that you just have to grind down on them.” It might be the tequila or the sex talk but he’s getting pretty horny.

“Oh and when your sucking dick and you take it really deep just before they come.” Dannee licks her lips and makes a slurping sound. “Drool everywhere mixed with come.” She wipes the corners of her mouth with the back of her hand.

“Lots of come.” Jensen insists as he downs another shot of Patron and sucks a lime.

As the night wears on, their talk gets more sexual. Dannee’s almost on Jensen’s lap, her legs spread wide exposing her thong that’s barely covering her dampening pussy. Jensen is turned on and he’s not entirely sure if it’s just the talk with the booze or he’s actually considering what a soft wet pussy surrounding his ridged hard-on might feel like.

They’re both pretty drunk by the time they order the cab and Jensen insists that Dannee stay with him tonight instead of going home.

Jensen stumbles into the bathroom to change after giving Dannee a t-shirt to wear. He’s changing into his pajama bottoms. His cock is still hard and he’s thinking about what his friend looks like naked. His hard-on isn’t going down at the thought and he just wonders if he really would like heterosexual sexing. 

Of course they sleep in the same bed when they have sleepovers. It’s never been an issue but when Jensen climbs into bed tonight the soft-scape of Danneel’s body under the sheets makes him feel a little uncomfortable.

So when Dannee snuggles in close and wraps her arms around him --like she always does-- he has to swallow hard. 

“So, Dannee,” he says quietly as if he doesn’t really want her to hear. “Are you horny?”

She giggles and snorts. “Tequila and sex talk with the hottest guy in the bar? Of course I’m wet, but it’s all good. I’ll just sleep it off because tomorrow the hangover will take care of it.”

Jensen laughs nervously before clearing his throat. “I could take care of it.” He’s still talking quietly.

She sits up on one elbow and looks at him. “What,” she can’t believe what she’s hearing. “I think I have the wrong parts or at least missing parts.”

“Maybe I’d like to try out some new parts.” He thinks he should be trying to convince himself and not her.

“Oh, baby.” She rubs his belly. “Are you having a drunken identity crisis?”

Jensen huffs. “No, just wondering if I might like a little pussy now and again too.” 

“Oh.” She smiles. “And you want to try it on my pussy?”

“Well, it is the one I’d be most likely to be attracted too if I did switch sides.” 

“That’s a tall order, to have the pussy that could turn a gay man straight.” 

“Not straight, maybe just bi.” 

She smiles up at him with drunken glassy eyes before slipping her hand under his t-shirt to finger her way up his sternum. Jensen hums at the feeling of her soft touches, he closes his eyes and tries to let the sensations wash over his sexually heat prickled skin.

She finds a nipple and gently pinches it, her nails scrape over the hard nub and Jensen flinches with the sharp scratch. “Sorry,” she whispers as she ghosts her lips over his chest.

“It’s okay.” He shifts her so that he’s hovering over her. He takes one of her breasts in his hand and palms it like a basketball. The soft mound gives under his rough grip. She moans at the feeling. “Mmmm, yeah, like that.” Her words are dark and husky. She slips a hand down and cradles his hard-on through the fabric of his pajama pants. He pushes into her touch but gets no friction; her soft hands knead at the stiff rod instead of stroking it. He bucks for more friction to no avail.

He’s shifting his attention from her breast to her belly. His hand smoothes over the soft taunt flesh feeling for hard muscles as he makes his way down to her hips where his thumbs instinctively look for the thick cut of hip bones to hold on to. He finds only soft curves and fleshy buttocks to cling to. _I can work with it._ he thinks as he presses into her body to find that sweet grind and friction. 

She’s pushing into his hand as he slips it across her pelvic bone, begging him to go lower but he doesn’t, he just squeezes her hips as he grinds into her thigh. She takes his wrist and guides it to her soft almost hairless mound. His fingers are thickly fumbling with the plump wet lips, not sure what to do with them. She rotates her hips and his fingers slip inside of them to find the extremely moist heat and hard bump between them. She moans when he slides over her clitoris.

“Ugh, yeah, now you’ve got it.” Her hips swivel showing him how to flick over it.

Jensen slides over the wetness feeling the folds and soft tissue swelling around his digits. He wants more, he can handle the feeling of her body but he needs more sensation on his cock. “Go under the pants,” he says breathlessly as he ruts against her body. 

“No problem.” Her hand shifts and yanks down the elastic waistband to expose his hard cock. She wraps her hand around it and starts to slide up and down over the stiffness. He bucks into her touch.

“Better,” He finds the pleasure spot on her body, she jerks and moans. Her hips buck and she feels even wetter than before. He figures he did something right. “Harder please,” he asks with need in his voice. She squeezes tighter as she strokes his dry cock.

Dannee slips out of Jensen’s reach and makes her way down to his cock. She pushes him onto his back and smiles up at him. “Relax, I am going to make you feel so good.” It’s a line he’s heard a thousand times before. She takes his dick into her mouth and starts going up and down on it. He holds her head, wants to push it down and make her deep-throat him since most men don’t have a gag reflex it’s not an issue but all the het stories he’s heard women have major gag reflexes, so he hold back and just tries to enjoy the wet heat of her mouth.

“Come up here,” he says after enduring the soft sloppy blow job as long as he could. He knows that plummeting into her soft cunt has to feel better than that blowjob. She climbs up his body with her mouth, stopping to suck on one of his nipples before nipping at the hollow of his neck. He rolls her onto her back and climbs between her now spread legs. She’s smiling up at him with long lashes, soft eyes and pink curled lips. He gives his cock a few rough strokes and the spits down on his palm to lube it up. She’s eager, her hips are canted and she’s kneading her own breasts. He looks down at the glistening slit then slips the head between it. 

She moans and rotates her hips, he slips up and down looking for the entrance and goes a little too far before hitting the soft pucker of her anus. She pulls back and gasps. “Not there, up a little more.” He looks horrified at her fear. It feels so natural to him to go there, to find pleasure in that tight heat but she already has a hole for that and it’s not her ass so he slips up just a little bit to find her gaping vaginal opening. She exhales and spreads her legs farther apart to accommodate his cock. He slips inside of the slippery wet heat and without any friction slides all way in and bottoms out. She squirms under him, her body moving with short thrusts as he starts to buck into her.

It’s wet and wide and not what he’s used to. He loves the tight squeeze of his lover’s ass, the pull when he draws out before shoving back in again. But he thinks he’s doing it right because she’s bucking and squirming on his cock.

“Ngh, there, no there,” she grunts out. She draws her knees up and hooks her ankles around his waist as she searches for better friction. His body is moving but he’s missing her gspot. She reaches between them and rubs at her clit and it helps. 

She’s exuberating wetness as Jensen’s pumping in and out of her, her body is squeezing his cock but not enough and he feels her hand between them. He’s thrusting in and out, working hard, trying to pleasure her and get himself off. It feels like they’ve been doing this for hours. She’s clutching his shoulders and using his body for leverage.

“Let me on top,” she moans, her legs releasing him. He obliges and rolls over taking her with him. She’s spread eagle over him, his cock still buried inside of her pussy. 

“Impressive.” She laughs.

“I’ve had practice flipping over while buried inside.” He lifts her up so that she’s sitting more comfortably over his hips.

“It shows.” She positions herself and starts moving up and down. His hips pushing up and thrusting her forward, she takes purchase with her palms on his chest.

They grind together, her body lifting up and slamming down onto his cock. She feels a twinge of electricity shoot through her as she comes a mini orgasm from stroking her own clit while riding him.

He’s sweating and tired but still no orgasm or sign of one to come. His cock isn’t ridged anymore and he’s barely holding on to enough erection to finish bringing her to orgasm. He closes he eyes and tries to think of the tight heat of a guy’s ass, how it makes him feel and how it feels to come hot into that snug heat. He can barely keep his hard-on even with these thoughts. The sight of her soft body bouncing on him does nothing for him and he hopes that she comes soon because he’s exhausted.

She finally falls forward panting, she’s tired and with her self induced mini orgasm, she’s satiated enough to fake enjoying the awkward sex with her best friend. “Oh, god,” She gushes as she peppers his chest with soft kisses.

He smiles as he pulls out of her body and lets his semi-hard cock relax. He strokes her back softly and cuddles her. “Did you come?” he asks, trying to be attentive.

“Yes,” she’s not really lying. “Enough.” She snuggles into his cradling arms.

And Jensen is undoubtedly sure now, no acceptations, no second guessing. He is indubitably gay.

The end


End file.
